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Synthesis of Spirooxindoles Bearing 1, 3‐Oxathiolane ‐2‐thione Moiety From Isatin‐Derived Propargylic Alcohols
Author(s) -
Kim Jae Nyoung,
Lee Sangku
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12206
Subject(s) - moiety , isatin , carbon disulfide , chemistry , alkoxide , xanthate , disulfide bond , stereochemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , biochemistry
Spirooxindoles bearing 1,3‐oxathiolane‐2‐thione moiety were synthesized from isatin‐derived propargylic alcohols and carbon disulfide in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU). The spirooxindoles were formed stereoselectively via attack of the alkoxide of propargylic alcohol to carbon disulfide to form xanthate anion and a following 5‐ exo‐dig cyclization process.